After a month in which Portland mostly abstained from political vandalism, protesters smashed windows in the tony Pearl District on Saturday evening during a protest of U.S. immigration policies.

At 8 pm on Feb. 27, over 100 black-clad activists gathered in The Fields Park—at the north edge of the Pearl District, home to some the city's most expensive high-rises and more than a mile from the downtown courthouses where most protests have occurred in the past year.

The reason? A protest of the treatment of undocumented people currently held in the custody of U.S. Immigration and Customs Enforcement and U.S. Customs and Border Protection. The target? A field office for U.S. Citizenship and Immigration Services, located four blocks away from the park.

That office is an obscure location; it had never been the target of a previous march. But its location in the Pearl District offered protesters new visibility from the windows of newly reopened restaurant dining rooms. Residents and restaurantgoers watched and filmed the protesters on their cellphones as the crowd marched past—the diners' faces a mixture of curiosity and worry.

A shattered window in the Pearl District. (Justin Yau)
A shattered window in the Pearl District. (Justin Yau)

The events that unfolded suggest that continued vandalism in Portland is not merely an overflow of anger, but a planned and fairly sophisticated operation by a small crew of activists. And the increased numbers of participants since the inauguration protests suggest that this may be the starting gun for a rejuvenated series of protests in 2021 as the weather and decreased COVID risks make public mass gatherings more permissible.

Most members of the crowd wore helmets, respirators and other protective equipment, expecting tear gas and other munitions to be used during dispersal operations by law enforcement. That never happened.

Upon arriving at the USCIS office, some members of the crowd began spray-painting the plywood panels of the boarded-up office while others provided cover from security cameras, using umbrellas and laser pointers. Protesters covered the sides of the building with slogans, such as "No Kids in Cages," and the names of "Breonna Taylor" and "Tete Gulley." Within minutes, the action was over.

Crowds departed south before turning back east presumably to return to The Fields Park. That's when Portland police on bicycles swept in from the rear of the march.

Portland bike cops intercept and corral protesters on Feb. 27, 2021. (Justin Yau)
Portland bike cops intercept and corral protesters on Feb. 27, 2021. (Justin Yau)

Officers pursued and corralled the crowd through the Pearl District. Some members of the crowd smashed windows of businesses and pushed over electric scooters during the pursuit. Windows from at least six businesses were cracked—a Chipotle, a Starbucks and a branch of Umpqua Bank—one private vehicle from Arcadia Security was vandalized.

The well-established distaste of protesters and police for each other was then displayed for the view of diners and other onlookers.

At 10:30 pm, a squad of Portland police bicycle officers charged the protesters. One bike cop collided with a videographer documenting the protest, sparking a heated verbal exchange between the two parties. Officers ordered protesters and passing bystanders alike to "Get off the streets or go to jail!"

Among them was an elderly bystander who did not wish to disclose his name. "Isn't the immigration building a few blocks over?" he asked, perplexed, surveying the damaged windows of the Urban Pantry convenience store. Like many liberal-leaning Portlanders, he didn't see a connection between anti-capitalist property destruction and anti-government protest (a link most protesters felt was intuitive, even obvious). Nor did he understand the forceful approach used by the Portland Police Bureau to stop the march.

Officers secured the intersection, but were quickly flanked by protesters on opposing sidewalks, who then verbally accosted the police: "You kamikazed the fucking crowd! Great deescalation, guys!"

Protesters continued to yell at the officers to "Move back!," eventually pushing them to withdraw from the scene. The protest eventually dwindled as the shrinking crowd continued wandering around the Pearl District, getting into sporadic arguments with local residents walking the streets or watching from their terraces. One inebriated, half-naked resident loudly traded profanities with the protesters gathered below from his second-story apartment before starting to pleasure himself in full view of the street. He disappeared from sight after protesters shined flashlights at him.

Police arrested 31-year-old Darrell Kimberlin for criminal mischief, and a 17-year-old minor for interfering with a peace officer.